US3853921A - Process for the preparation of 3-cyanochromones - Google Patents
Process for the preparation of 3-cyanochromones Download PDFInfo
- Publication number
- US3853921A US3853921A US00312155A US31215572A US3853921A US 3853921 A US3853921 A US 3853921A US 00312155 A US00312155 A US 00312155A US 31215572 A US31215572 A US 31215572A US 3853921 A US3853921 A US 3853921A
- Authority
- US
- United States
- Prior art keywords
- mole
- cyanochromones
- percent
- hydroxylamine
- solid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- SFWNPLLGXKJESA-UHFFFAOYSA-N 4-oxochromene-3-carbonitrile Chemical class C1=CC=C2C(=O)C(C#N)=COC2=C1 SFWNPLLGXKJESA-UHFFFAOYSA-N 0.000 title abstract description 5
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 235000019253 formic acid Nutrition 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 7
- 239000001257 hydrogen Substances 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical group 0.000 abstract description 6
- 150000002431 hydrogen Chemical group 0.000 abstract description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 5
- FSMYWBQIMDSGQP-UHFFFAOYSA-N 4-oxochromene-3-carbaldehyde Chemical class C1=CC=C2C(=O)C(C=O)=COC2=C1 FSMYWBQIMDSGQP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003266 anti-allergic effect Effects 0.000 abstract description 3
- BVPWJMCABCPUQY-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 BVPWJMCABCPUQY-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000043 antiallergic agent Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000002731 stomach secretion inhibitor Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004280 Sodium formate Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 6
- 235000019254 sodium formate Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CCUIZOSFSPCGLS-UHFFFAOYSA-N 3-(hydroxymethyl)chromen-4-one Chemical class C1=CC=C2C(=O)C(CO)=COC2=C1 CCUIZOSFSPCGLS-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- PCEZXSJBHMOQFT-UHFFFAOYSA-N 6-bromo-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(Br)=CC=C21 PCEZXSJBHMOQFT-UHFFFAOYSA-N 0.000 description 1
- MGVVCEKLWMZFLS-UHFFFAOYSA-N 6-bromo-4-oxochromene-3-carbonitrile Chemical compound O1C=C(C#N)C(=O)C2=CC(Br)=CC=C21 MGVVCEKLWMZFLS-UHFFFAOYSA-N 0.000 description 1
- CKEDZWWMONCZLW-UHFFFAOYSA-N 8-methoxy-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=C1C(OC)=CC=C2 CKEDZWWMONCZLW-UHFFFAOYSA-N 0.000 description 1
- RWYNFTSXZRBELM-UHFFFAOYSA-N 8-methoxy-4-oxochromene-3-carbonitrile Chemical compound O1C=C(C#N)C(=O)C2=C1C(OC)=CC=C2 RWYNFTSXZRBELM-UHFFFAOYSA-N 0.000 description 1
- 206010052613 Allergic bronchitis Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- PCIITXGDSHXTSN-UHFFFAOYSA-N Chromone-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)=COC2=C1 PCIITXGDSHXTSN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Definitions
- R is hydrogen, halogen, or lower alkoxy.
- the alkyl portion of alkoxy is meant to include lower aliphatic hydrocarbons having from one to seven carbon atoms in the carbon chain, preferably those having one to four carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl or isobutyl.
- the compounds prepared by the process of this invention may be combined with a parenterally acceptable vehicle such as a gum tragacanth saline suspension, to provide dosage forms suitable for parenteral administration; or they may be combined with pharmaceutical diluents such as lactose, cornstarch, microcrystalline cellulose, Polyethylene Glycol 4,000 and/or 6,000, and the like, and formulated into tablet or capsule dosage form.
- a parenterally acceptable vehicle such as a gum tragacanth saline suspension
- pharmaceutical diluents such as lactose, cornstarch, microcrystalline cellulose, Polyethylene Glycol 4,000 and/or 6,000, and the like, and formulated into tablet or capsule dosage form.
- a dose of 50 mg orally, or by inhalation in the form of an aerosol spray is prescribed to give symptomatic relief of asthma.
- the therapeutic spectrum of these compounds may be broadened by combining them with sympathomimetic agents such as isoproterenol or with steroids such as cortisone and its derivatives.
- the compounds prepared by the process of this invention also exhibit anti-secretory effects and gastric anti-ulcer activity in experimental animals such as rats.
- experimental animals such as rats.
- they when they are tested according to the procedure according to H. Shay, et al., Gastroemerology: 5, 43 (1945), in the pylorus ligated rat they exhibit an ED of 20 mg to 50 mg/kg per body weight.
- the compounds prepared by the process of this invention are useful as intermediates for the production of other chromone derivatives. For example, they undergo solvolysis reaction to give those compounds having the following formula:
- X is hydrogen or lower alkyl and R, is hydrogen, halogen, or lower alkoxy (with lower alkyl and wherein R represents hydrogen, halogen, or lower alkoxy, in accordance with the following reaction scheme:
- Compound 11 is refluxed together with hydroxylamine or a salt thereof, in the presence of sodium formate, using formic acid as the solvent.
- hydroxylamine hydrochloride is used in a 10 to 20 percent excess over the stoichiometric amount needed for reaction with the 3-formylchromone starting material.
- the sodium formate is added in excess, based on the amount of hydroxylamine.
- the reaction is conducted in reflux temperature, i.e., at C.
- Starting Compound 1 is prepared by oxidizing 3- (hydroxymethyl) chromones with an oxidizing agent, such as sodium dichromate with glacial acetic acid, concentrated nitric acid or potassium persulfate.
- an oxidizing agent such as sodium dichromate with glacial acetic acid, concentrated nitric acid or potassium persulfate.
- the 3-(hydroxymethyl)chromones are prepared in accordance with the description set forth in co-pending U.S. application Ser. No. 309,329 filed Nov. 1972, now U.S. Pat. No. 3,798,240 issued Mar. 19, 1974.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00312155A US3853921A (en) | 1972-12-04 | 1972-12-04 | Process for the preparation of 3-cyanochromones |
| DE2356901A DE2356901A1 (de) | 1972-12-04 | 1973-11-14 | Verfahren zur herstellung von 3cyanochromonen |
| GB5439373A GB1402226A (en) | 1972-12-04 | 1973-11-23 | 3-cyanochromones |
| AU63096/73A AU474118B2 (en) | 1972-12-04 | 1973-11-30 | Process forthe preparation of 3-cyanpchromones |
| CA187,150A CA995682A (en) | 1972-12-04 | 1973-12-03 | Process for the preparation of 3-cyanochromones |
| JP13567273A JPS5310595B2 (en, 2012) | 1972-12-04 | 1973-12-03 | |
| FR7343284A FR2208896B1 (en, 2012) | 1972-12-04 | 1973-12-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00312155A US3853921A (en) | 1972-12-04 | 1972-12-04 | Process for the preparation of 3-cyanochromones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3853921A true US3853921A (en) | 1974-12-10 |
Family
ID=23210120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00312155A Expired - Lifetime US3853921A (en) | 1972-12-04 | 1972-12-04 | Process for the preparation of 3-cyanochromones |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3853921A (en, 2012) |
| JP (1) | JPS5310595B2 (en, 2012) |
| AU (1) | AU474118B2 (en, 2012) |
| CA (1) | CA995682A (en, 2012) |
| DE (1) | DE2356901A1 (en, 2012) |
| FR (1) | FR2208896B1 (en, 2012) |
| GB (1) | GB1402226A (en, 2012) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932466A (en) * | 1974-12-13 | 1976-01-13 | Warner-Lambert Company | Substituted 2-amino chromones and process for the preparation thereof |
| US4008252A (en) * | 1973-04-18 | 1977-02-15 | Warner-Lambert Company | Substituted-3-formylchromone derivatives |
| US4013771A (en) * | 1975-12-15 | 1977-03-22 | Warner-Lambert Company | Substituted 2-aminothiochromones |
| US4018798A (en) * | 1975-11-20 | 1977-04-19 | Warner-Lambert Company | Substituted (4-oxo-4H-1-benzopyran-2-yl)cyclopropane carboxylic acids and esters |
| US4024160A (en) * | 1974-12-13 | 1977-05-17 | Warner-Lambert Company | Substituted 2-amino chromones and process for the preparation thereof |
| US4151180A (en) * | 1972-04-12 | 1979-04-24 | Takeda Chemical Industries, Ltd. | Chromone derivatives |
| US4196128A (en) * | 1978-12-13 | 1980-04-01 | Warner-Lambert Company | Process for the preparation of 3-cyanochromones |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6040067A (ja) * | 1983-08-15 | 1985-03-02 | テルモ株式会社 | 医療用容器 |
| FR3139311B1 (fr) | 2022-09-06 | 2024-07-19 | Psa Automobiles Sa | Procédé et dispositif de présentation de la longueur d’un d’objet dépassant de l’arrière d’un véhicule automobile |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701254A (en) * | 1952-06-20 | 1955-02-01 | Basf Ag | Production of isochromanylacetic acids and their derivatives |
| US3484445A (en) * | 1965-12-21 | 1969-12-16 | Fisons Pharmaceuticals Ltd | Derivatives of chromone-2-carboxylic acid |
| US3767679A (en) * | 1971-09-13 | 1973-10-23 | Warner Lambert Co | 3-substituted chromones |
-
1972
- 1972-12-04 US US00312155A patent/US3853921A/en not_active Expired - Lifetime
-
1973
- 1973-11-14 DE DE2356901A patent/DE2356901A1/de active Pending
- 1973-11-23 GB GB5439373A patent/GB1402226A/en not_active Expired
- 1973-11-30 AU AU63096/73A patent/AU474118B2/en not_active Expired
- 1973-12-03 JP JP13567273A patent/JPS5310595B2/ja not_active Expired
- 1973-12-03 CA CA187,150A patent/CA995682A/en not_active Expired
- 1973-12-04 FR FR7343284A patent/FR2208896B1/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701254A (en) * | 1952-06-20 | 1955-02-01 | Basf Ag | Production of isochromanylacetic acids and their derivatives |
| US3484445A (en) * | 1965-12-21 | 1969-12-16 | Fisons Pharmaceuticals Ltd | Derivatives of chromone-2-carboxylic acid |
| US3767679A (en) * | 1971-09-13 | 1973-10-23 | Warner Lambert Co | 3-substituted chromones |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4151180A (en) * | 1972-04-12 | 1979-04-24 | Takeda Chemical Industries, Ltd. | Chromone derivatives |
| US4008252A (en) * | 1973-04-18 | 1977-02-15 | Warner-Lambert Company | Substituted-3-formylchromone derivatives |
| US3932466A (en) * | 1974-12-13 | 1976-01-13 | Warner-Lambert Company | Substituted 2-amino chromones and process for the preparation thereof |
| US4024160A (en) * | 1974-12-13 | 1977-05-17 | Warner-Lambert Company | Substituted 2-amino chromones and process for the preparation thereof |
| US4018798A (en) * | 1975-11-20 | 1977-04-19 | Warner-Lambert Company | Substituted (4-oxo-4H-1-benzopyran-2-yl)cyclopropane carboxylic acids and esters |
| US4013771A (en) * | 1975-12-15 | 1977-03-22 | Warner-Lambert Company | Substituted 2-aminothiochromones |
| US4196128A (en) * | 1978-12-13 | 1980-04-01 | Warner-Lambert Company | Process for the preparation of 3-cyanochromones |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2208896A1 (en, 2012) | 1974-06-28 |
| GB1402226A (en) | 1975-08-06 |
| JPS4986377A (en, 2012) | 1974-08-19 |
| FR2208896B1 (en, 2012) | 1980-10-10 |
| CA995682A (en) | 1976-08-24 |
| AU6309673A (en) | 1975-06-05 |
| AU474118B2 (en) | 1976-07-15 |
| DE2356901A1 (de) | 1974-06-27 |
| JPS5310595B2 (en, 2012) | 1978-04-14 |
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